Synthesis, structure, and spectral, electrochemical and fluoride sensing properties of meso-pyrrolyl boron dipyrromethene

Dalton Transactions : an International Journal of Inorganic Chemistry
Booruga UmasekharMangalampalli Ravikanth

Abstract

meso-Pyrrolyl boron dipyrromethene (BODIPY) was prepared under simple reaction conditions by using commercially available chemicals. Prior to this work, the BODIPY compound was prepared in multiple steps by using precursors which were not readily available. The X-ray structure of BODIPY revealed that the meso-pyrrole ring is tilted towards the BF2-dipyrrin moiety with a dihedral angle of 33.94°. The reactivity of the meso-pyrrole ring of BODIPY was tested by subjecting it to bromination and formylation reactions, which afforded (α-bromopyrrolyl) BODIPY and (α-formylpyrrolyl) BODIPY in decent yields. The (α-formylpyrrolyl) BODIPY was used to prepare the pyrrole bridged BODIPY dyad. The pyrrole bridged BODIPY dyad exhibited a 15-20 nm bathochromic shift in the absorption band and was weakly fluorescent compared to meso-pyrrolyl BODIPY. Furthermore, our studies show that the meso-pyrrolyl BODIPY can be used as a specific sensor for F(-) ions because of the presence of meso-pyrrole NH which is involved in interactions with F(-) ions. To prove that meso-pyrrole NH is involved in sensing F(-) ions, we also prepared meso-(N-methylpyrrolyl)-BODIPY and characterized it by various spectroscopic techniques and crystallography. Our studies...Continue Reading

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Citations

Jan 6, 2016·Luminescence : the Journal of Biological and Chemical Luminescence·Qianmin MaQianming Wang
Apr 15, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Koichi KatayamaYoshio Teki
Jul 11, 2018·Topics in Current Chemistry·Toshiaki Murai
Sep 5, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Meifang LiuYulan Chen
Dec 5, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bruno F O NascimentoTeresa M V D Pinho E Melo

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